Potassium Carbonate → [3-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)-1,2,4-oxadiazol-5-yl]methanol

HRID 1644871Notes

Reaction equation

HRID 1644871 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:41])([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:29][N:28]=3)[CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[N:13]=1)(=O)C.C(=O)(O)[O-].[Na+]>O.CO>[CH3:41][C:23]([C:20]1[CH:21]=[CH:22][C:17]([C:14]2[N:13]=[C:12]([CH2:11][OH:10])[O:16][N:15]=2)=[CH:18][CH:19]=1)([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[CH:29][N:28]=1)[CH:24]([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 57910807[3-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)-1,2,4-oxadiazol-5-yl]methyl acetate

Product 1

HCID 57910795[3-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)-1,2,4-oxadiazol-5-yl]methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (743 mg, 5.38 mmol) in water (1.00 mL) was added to a stirred solution of 3c (0.896 mmol) in MeOH (3.00 mL) at rt. After approximately 1 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with water, brine, dried (sodium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-6% MeOH/DCM as eluent) to furnish the title compound 3d. m/z (ES) 431 (MH)+. 1HNMR (500 MHz, CD3OD): δ 8.55 (d, 1H, J=3.3 Hz), 8.28 (d, 1H, J=2.7 Hz), 7.94 (d, 2H, J=8.5 Hz), 7.88 (dt, 1H, J=1.7, 7.7 Hz), 7.61 (d, 1H, J=7.8 Hz), 7.48 (d, 2H, J=8.5 Hz), 7.35 (m, 3H), 5.23 (s, 2H), 3.08 (m, 1H, J=6.6 Hz), 1.70 (s, 3H), 0.86 (d, 3H, J=6.6 Hz), 0.80 (d, 3H, J=6.6 Hz).

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-6% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-ccded3786a774244bab76ec22351288f
Source dataset
uspto-grants-2012_02
Patent number
US08124628B2

Reaction notes

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